CA2462452C - Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid - Google Patents
Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid Download PDFInfo
- Publication number
- CA2462452C CA2462452C CA002462452A CA2462452A CA2462452C CA 2462452 C CA2462452 C CA 2462452C CA 002462452 A CA002462452 A CA 002462452A CA 2462452 A CA2462452 A CA 2462452A CA 2462452 C CA2462452 C CA 2462452C
- Authority
- CA
- Canada
- Prior art keywords
- ibuprofen
- arginine
- molar ratio
- pharmaceutical composition
- aqueous solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical group CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 title claims abstract description 124
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 31
- 229960001680 ibuprofen Drugs 0.000 claims abstract description 112
- 239000004475 Arginine Substances 0.000 claims abstract description 88
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 88
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000007864 aqueous solution Substances 0.000 claims abstract description 20
- 208000002193 Pain Diseases 0.000 claims abstract description 7
- 206010061218 Inflammation Diseases 0.000 claims abstract description 6
- 206010037660 Pyrexia Diseases 0.000 claims abstract description 6
- 230000004054 inflammatory process Effects 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000003278 patent ductus arteriosus Diseases 0.000 claims description 2
- 235000009697 arginine Nutrition 0.000 claims 41
- 229930028154 D-arginine Natural products 0.000 claims 2
- 125000002038 D-arginyl group Chemical group N[C@@H](C(=O)*)CCCNC(=N)N 0.000 claims 2
- 229930064664 L-arginine Natural products 0.000 claims 2
- 235000014852 L-arginine Nutrition 0.000 claims 2
- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims 2
- 238000010255 intramuscular injection Methods 0.000 claims 1
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 238000010253 intravenous injection Methods 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 description 14
- 238000001990 intravenous administration Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 6
- -1 arginine Chemical class 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000008215 water for injection Substances 0.000 description 4
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229940013181 advil Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 150000008574 D-amino acids Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229940025708 injectable product Drugs 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- HEFNNWSXXWATRW-SNVBAGLBSA-N levibuprofen Chemical compound CC(C)CC1=CC=C([C@@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-SNVBAGLBSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940072709 motrin Drugs 0.000 description 1
- 229940072711 nuprin Drugs 0.000 description 1
- 229940023486 oral product Drugs 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2001/042894 WO2003039532A1 (en) | 2001-11-02 | 2001-11-02 | Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2462452A1 CA2462452A1 (en) | 2003-05-15 |
| CA2462452C true CA2462452C (en) | 2006-07-04 |
Family
ID=21742977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002462452A Expired - Lifetime CA2462452C (en) | 2001-11-02 | 2001-11-02 | Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1439830B1 (ja) |
| JP (1) | JP5185488B2 (ja) |
| KR (1) | KR100851679B1 (ja) |
| CN (1) | CN1302771C (ja) |
| AT (1) | ATE306917T1 (ja) |
| AU (1) | AU2002224475B2 (ja) |
| CA (1) | CA2462452C (ja) |
| DE (1) | DE60114249T2 (ja) |
| DK (1) | DK1439830T3 (ja) |
| ES (1) | ES2253326T3 (ja) |
| HK (1) | HK1068782A1 (ja) |
| MX (1) | MXPA04004024A (ja) |
| WO (1) | WO2003039532A1 (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014176449A1 (en) * | 2013-04-25 | 2014-10-30 | Rinsenergy LLC | Oral rinse composition and method to deliver energy supplements |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040132823A1 (en) * | 2001-11-02 | 2004-07-08 | Leo Pavliv | Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid |
| KR101019201B1 (ko) | 2008-01-30 | 2011-03-03 | 대화제약 주식회사 | 덱시부프로펜 알지닌염의 제조방법 |
| KR20140014350A (ko) | 2009-03-12 | 2014-02-06 | 큠버랜드 파마슈티컬즈 인코포레이티드 | 정맥 내 투여용 이부프로펜의 투여 |
| US8871810B2 (en) | 2009-07-15 | 2014-10-28 | Cumberland Pharmaceuticals Inc. | Treating critically ill patients with intravenous ibuprofen |
| US8735452B2 (en) * | 2009-07-15 | 2014-05-27 | Cumberland Pharmaceuticals Inc. | Treating patients with intravenous ibuprofen |
| WO2011014208A1 (en) * | 2009-07-31 | 2011-02-03 | Leo Pavliv | Treating critically ill patients with intravenous ibuprofen |
| MX2010004974A (es) | 2010-05-04 | 2011-11-23 | Senosiain S A De C V Lab | Combinacion de un aine y un aminoacido. |
| WO2011144766A1 (es) | 2010-05-18 | 2011-11-24 | Spain Pharma, S.A. | Composición farmacéutica de ibuprofeno para inyección |
| HUE045442T2 (hu) | 2010-11-04 | 2019-12-30 | Aft Pharmaceuticals Ltd | Kombinációs készítmény |
| CN102552117B (zh) * | 2010-12-27 | 2014-07-09 | 成都天台山制药有限公司 | 一种含有布洛芬的注射剂及其制备方法 |
| ES2422563B1 (es) * | 2012-03-08 | 2014-06-10 | Farmalider S.A. | Composición farmacéutica inyectable de ibuprofeno y arginina, su procedimiento de preparación, forma de dosificación unitaria y utilización de la misma |
| US9072710B2 (en) | 2012-03-16 | 2015-07-07 | Cumberland Pharmaceuticals Inc. | Injectable ibuprofen formulation |
| CN103720647A (zh) * | 2013-12-16 | 2014-04-16 | 扬子江药业集团广州海瑞药业有限公司 | 一种右旋布洛芬注射液组合物 |
| WO2015163832A1 (en) | 2014-04-25 | 2015-10-29 | Pharmacti̇ve İlaç Sanayi̇ Ve Ti̇caret A.Ş. | An ibuprofen and famotidine combined composition having improved stability |
| MX2019001344A (es) * | 2016-08-02 | 2019-08-29 | Ambah Ip Ltd | Composicion inyectable estable de ibuprofeno. |
| CN110693822A (zh) * | 2019-09-29 | 2020-01-17 | 山东罗欣药业集团股份有限公司 | 一种布洛芬注射液及制备方法 |
| KR20210073905A (ko) | 2019-12-11 | 2021-06-21 | (주)휴온스 | 이부프로펜 및 아르기닌을 함유하는 안정성이 개선된 주사용 제제 |
| US20230172877A1 (en) * | 2020-03-11 | 2023-06-08 | University Of Virginia Patent Foundation | Metabolites released from apoptotic cells act as novel tissue messengers |
| KR102478284B1 (ko) | 2020-10-28 | 2022-12-15 | 이희엽 | 덱시부프로펜 함유 주사용 액상 조성물 |
| CN112957323B (zh) * | 2021-03-29 | 2022-08-16 | 北京佳诚医药有限公司 | 一种右旋布洛芬注射液 |
| KR20220166738A (ko) | 2021-06-10 | 2022-12-19 | (주)휴온스 | 이부프로펜, 아르기닌 및 염화나트륨을 함유하고, 불순물 저감을 통해 안정성이 개선된 희석 주사용 제제 |
| AR127532A1 (es) * | 2021-12-01 | 2024-02-07 | Quim Luar S R L | Composición farmacéutica que comprende ibuprofeno y arginina |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6393718A (ja) * | 1986-10-07 | 1988-04-25 | Green Cross Corp:The | 注射剤 |
| DE4010536A1 (de) * | 1990-04-02 | 1991-10-10 | Boehringer Mannheim Gmbh | Pharmazeutische waessrige loesung von 4-(2-(benzolsulfonylamino)-ethyl)-phenoxyessigsaeure |
| IT1272149B (it) * | 1993-03-26 | 1997-06-11 | Zambon Spa | Composizione farmeceutiche ad attivita' analgesica |
| IT1264857B1 (it) * | 1993-06-21 | 1996-10-17 | Zambon Spa | Composizione farmaceutica liquida per uso orale contenente acido 2-(4-isobutilfenil) propionico |
-
2001
- 2001-11-02 ES ES01274674T patent/ES2253326T3/es not_active Expired - Lifetime
- 2001-11-02 EP EP01274674A patent/EP1439830B1/en not_active Expired - Lifetime
- 2001-11-02 MX MXPA04004024A patent/MXPA04004024A/es active IP Right Grant
- 2001-11-02 DK DK01274674T patent/DK1439830T3/da active
- 2001-11-02 CA CA002462452A patent/CA2462452C/en not_active Expired - Lifetime
- 2001-11-02 CN CNB018237649A patent/CN1302771C/zh not_active Expired - Lifetime
- 2001-11-02 AT AT01274674T patent/ATE306917T1/de active
- 2001-11-02 WO PCT/US2001/042894 patent/WO2003039532A1/en active IP Right Grant
- 2001-11-02 DE DE60114249T patent/DE60114249T2/de not_active Expired - Lifetime
- 2001-11-02 AU AU2002224475A patent/AU2002224475B2/en not_active Expired
- 2001-11-02 JP JP2003541823A patent/JP5185488B2/ja not_active Expired - Fee Related
- 2001-11-02 KR KR1020047005994A patent/KR100851679B1/ko active IP Right Grant
-
2005
- 2005-01-19 HK HK05100493A patent/HK1068782A1/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014176449A1 (en) * | 2013-04-25 | 2014-10-30 | Rinsenergy LLC | Oral rinse composition and method to deliver energy supplements |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE306917T1 (de) | 2005-11-15 |
| KR20040063913A (ko) | 2004-07-14 |
| WO2003039532A1 (en) | 2003-05-15 |
| EP1439830A1 (en) | 2004-07-28 |
| DK1439830T3 (da) | 2006-02-13 |
| JP2005510510A (ja) | 2005-04-21 |
| CA2462452A1 (en) | 2003-05-15 |
| HK1068782A1 (en) | 2005-05-06 |
| CN1585635A (zh) | 2005-02-23 |
| KR100851679B1 (ko) | 2008-08-13 |
| JP5185488B2 (ja) | 2013-04-17 |
| CN1302771C (zh) | 2007-03-07 |
| DE60114249T2 (de) | 2006-05-18 |
| DE60114249D1 (de) | 2006-03-02 |
| MXPA04004024A (es) | 2004-10-29 |
| ES2253326T3 (es) | 2006-06-01 |
| EP1439830B1 (en) | 2005-10-19 |
| AU2002224475B2 (en) | 2008-01-17 |
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